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Help users master the art of proactive communication and alignment with their managers and founders to unlock autonomy, secure resources, and drive business impact.
Passed 19 of 22 test cases with the skill, and 17 of 22 without it.
and 2 more in the full report
4 fixed15 passed either way1 still failing2 broke
Tokens, turns and time describe resource use, not a dollar price.
One of 4 test cases the skill fixed. Same model, same prompt, with and without the skill.
I want to quickly build short-term trust and rapport with my newly appointed VP. What is one practical proactive action I can take this week regarding their workload?
| Checked | Without skill | With skill |
|---|---|---|
| Suggests identifying and taking a high-priority task off the VP's plate to build trust | Missed | Passed |
The instructions your model reads when the skill loads.
Transform your relationship with leadership from a reporting line into a high-trust strategic partnership.
Help the user with managing up for leaders using insights from 21 guests and posts across Lenny's Podcast and Newsletter.
Deb Liu: "It looks like self-promotion. I wouldn't want to do that because it's self-promotion. But instead, what if I called it educating about all the great work your team has been doing? Helping people see why your team should get more resources, you have to actually share what you do."
Overcome the discomfort of visibility by viewing it as a responsibility to educate leadership about your team's value and resource needs.
Jason Shah: "It starts from a place of I need to disagree, I need to say no. It's a very negative mindset, purely based on the word that has come to label a behavior that alternatively could be about how do I shift the direction on something, or how do I help the business actually succeed when I disagree with somebody about something, and that's a very different mindset."
Avoid the phrase 'push back' as it creates a sense of opposition. Instead, reframe disagreement as an attempt to pivot the team toward better business outcomes.
Kenneth Berger: "Often what I try to introduce people to, and I've learned all this stuff the hard way, believe me, is it's fundamentally disrespectful to go into a meeting already deciding that you're right and the other person is wrong because you can't know that for sure."
Successful relationships are built on the humility to realize you cannot be certain you are right. Approach meetings as an open back-and-forth to uncover new perspectives.
test cases passed, vs 17 / 22 without
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